JPH10195168A - Polymer resin and method for coloring product made therefrom - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a polyurethane which can be colored with a disazo coloring agent bound through a covalent bond in the polyurethane by mixing a polyol, a polyisocyanate, a catalyst, and a disazo coloring agent having poly(oxyalkylene) substituents bound to each end of disazo chromophore and polymerizing the mixture. SOLUTION: A polyol is mixed with a polyisocyanate, a catalyst, and a disazo coloring agent having poly(oxyalkylene) substituents each of which is bound to each end of disazo chromophore and has 2 to 200 alkylene oxide residues and nucleophilic terminal groups capable of reacting with a polyisocyanate, and the mixture is polymerized. The coloring agent used preferably comprises one whose poly(oxyalkylene) substituents each comprises a random or block copolymer of ethylene oxide and propylene oxide, contains 4-75 alkylene oxide residues and has terminal hydroxyl groups.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a method for coloring a polymer resin with a reactive poly (oxyalkylene) substituted disazo colorant, in particular a disazo colorant incorporated into the backbone of polyurethane resins. .

[0002]

The use of poly (oxyalkylene) substituted colorants in thermosetting resins is well known,
The following references can be found: Cross et al., US Pat. No. 4,284,729; Kluger et al., US Pat.
Kluger et al., 4,751,254; Kluger
U.S. Pat. No. 4,761,502; Kluger et al., U.S. Pat. No. 4,775,748; Rekers et al., U.S. Pat.
846; Kluger et al., U.S. Patent 4,912,203 and Mach.
ell et al., US Patent 5,231,135.

[0003] In subsequent developments, the reactivity of the colorant was enhanced by obtaining branched poly (oxyalkylene) chains, each having a plurality of reactive end groups. Branching was facilitated by introducing glycidol or chloropropanediol into the poly (oxyalkylene) substituent. Examples of branched reactive colorants can be found in the following literature: Kluger et al.
U.S. Pat. No. 5,082,938 and Moody et al., U.S. Pat. No. 5,290,921. These colorants are highly reactive and therefore have poor extractability, which is a disadvantage for their use.
Glycidol is a relatively expensive raw material, the use of which significantly increases the cost of the product. In addition, in some applications, it is desirable to place a limit on the viscosity of the colorant, with branched poly (oxyalkylene) chains tending to increase the viscosity.

[0004] Typically, reactive colorant production lines for polymer resins contain three to five "primary" colorants that are blended to visually match any desired shade. . In one prior art, the primary colorant is
Poly (oxyalkylene) -substituted orange monoazo colorant. Orange colorants provide good color space and tone stability, but the intermediates used in the synthesis are costly and not readily available.

[0005] Poly (oxyalkylene) substituted bisazo colorants for use as temporary colorants are known as Hi
Nes et al., US Pat. No. 5,108,460 and Hauser et al., US Pat. No. 4,113,721. The poly (oxyalkylene) substituent imparts water solubility to the colorant. Temporary colorants are a way to identify and classify fibers, by temporarily coloring yarn during fabric production,
It can also be used as a way to facilitate the repair of broken yarns. The temporary colorant is later washed from the fabric prior to dyeing and finishing.

[0006]

Accordingly, it is an object of the present invention to provide a method of coloring a polymer resin with a poly (oxyalkylene) substituted disazo colorant with improved reactivity. Another object is to increase the reactivity of the colorant without the need for expensive epoxides such as glycidol. Yet another object is to minimize the colorant viscosity. Another object is to provide a disazo orange colorant that meets the above objects. Yet another object of the present invention is to provide a colorant for use in polyurethane systems.

[0007]

Accordingly, blending a disazo colorant with a monomer mixture, wherein the colorant has a poly (oxyalkylene) substituent at each end,
The substituent contains from 2 to 200 alkylene oxide residues and has a nucleophilic end group that can react with some of the monomers. And a method of coloring a polymer resin having the step of subjecting the mixture of disazo and colorant to conditions under which the monomer and disazo colorant polymerize to form a colored polymer resin. The monomers may comprise one, two or more reactive species, such as polyols and polyisocyanates. The disazo colorant is first dissolved or suspended in one type of monomer,
Thereafter, a mixture of polymerizable monomers is formed by adding a second reactive species.

[0008] The appropriate reaction conditions for the monomer mixture are not significantly changed by the addition of the disazo colorant. Thus, those skilled in the art of synthesizing polymers will appreciate the ratio of reactants (monomer), pH, temperature, pressure, duration, addition of reactants, such that the disazo colorant is copolymerized or grafted with the monomers. The reaction conditions can be readily selected, such as the order, solvents, catalysts and processing aids that help promote the polymerization.

In addition to achieving the above objects, preferred embodiments of the present invention have one or more of the following features and advantages.

The colorant is liquid at ambient conditions; the colorant is present during the polymerization of the resin and is covalently bound to the polymer; It is not so easily extracted from the polymer. -The poly (oxyalkylene) substituent of the disazo colorant is not branched. Disazo colorants are substantially less viscous than prior art colorants, despite having poly (oxyalkylene) substituents at each end. -The disazo colorant can be dissolved up to 1 wt% in at least one monomer species forming a polymerizable monomer mixture. -The colorant is incorporated into the backbone of the polymer resin. -The colorant is grafted to the polymer resin. -The polymer resin is a polyurethane resin.

[0011]

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Without limiting the scope of the invention, preferred embodiments and features are described below. Unless otherwise indicated, all parts and percentages are by weight,
The conditions are the ambient environment, that is, a pressure of 1 atmosphere and 25 ° C.
The term aromatic compound is an unsaturated heterocyclic compound containing one or two fused unsaturated hydrocarbon rings and one to three heteroatoms selected from S, N and O,
Means that can be benzo-condensed. Unless otherwise stated, aliphatic hydrocarbons are 1 to 12 carbon atoms in length, and cycloaliphatic hydrocarbons contain 3 to 8 carbon atoms. The terms aryl and alkylene are intended to be limited to monocyclic and fused bicyclic unsaturated hydrocarbons.

All of the US patents mentioned herein are:
Part of this specification is incorporated by reference.

[0013] The colored polymer resin may be prepared by a method of polymerizing a monomer mixture incorporating a reactive poly (alkylene) substituted disazo colorant into the mixture.

The disazo colorants of the present invention are characterized by two azo groups covalently linked in a straight line.
Each diazo group is covalently linked to two aromatic groups.
These azo groups can be linked together to a bifunctional aromatic group. That is, these are separate aromatic groups (the aromatic groups are
Tied together. ) Can be bound from the inside of the disazo chain. On the inner, opposite side of the disazo chain, each azo group is attached to an aromatic group, both of which are referred to as outer aromatic groups.

Disazo colorants include (1) primary disazo colorants, such as symmetric and asymmetric compounds obtained from symmetric and asymmetric compounds having a tetraazo component and a difunctional coupling component; (2) secondary disazo colorants. A colorant, for example, a compound prepared by diazotizing an aminoazo compound where the amino group is derived from a first coupling component and then coupling with a second coupling component; and (3) a separated conjugated azo Includes disazo colorants made by incorporating the system into a single molecule, for example, by condensing an aminoazo compound with phosgene, cyanuric chloride or fumaric dichloride.

When the inside of the disazo colorant contains separate aromatic groups, the aromatic groups are covalently bonded to each other by
Alternatively, they may be linked by a divalent group. Examples of suitable divalent linking _{groups, O, S, CO 2,} C 1-8 alkylene, C _2-8 alkenylene, carbonyl, triazine, -C (O) CH = C
HC (O)-, phenylene, -C (O) NH- and -N
HC (O) NH- is included. In addition, the divalent linking group of the disazo colorant of the present invention can be referred to as “Color Index (Colo
r Index) "Third Edition, Volume 4, C.I. I. Number 20000
29999, pp. 4139-4276 (1971).

The disazo colorant further has at least one poly (oxyalkylene) substituent attached to each terminal, preferably outer, aromatic group of the colorant. The number of poly (oxyalkylene) substituents varies from 1 to 6, preferably from 1 to 4, per aromatic group.

Poly (oxyalkylene) substituents are characterized as linear or branched C ₂ -C ₄ alkylene oxides, predominantly from 2 to 200 residues of ethylene oxide and propylene oxide residues. Small amounts of glycidol, butylene oxide and other compatible monomers are also incorporated into the substituents. For example, glycidol monomers are incorporated into poly (oxyalkylene) substituents to promote branching. If it is desired to increase the branching, preferably 2 to 10 glycidol units are provided per poly (oxyalkylene) chain. In a preferred embodiment, the poly (oxyalkylene) substituent contains predominantly 2 to 75, most preferably 4 to 35 residues of ethylene oxide or random and block copolymers thereof.

The poly (oxyalkylene) substituent has a nucleophilic end group. The end groups are capable of reacting with monomers that form a polymer resin that can be colored. One skilled in the art will recognize that the group may vary depending on the monomer used. For example, the polyol / polyisocyanate, poly end groups (oxyethylene) substituents, -OH, -NH ₂ or SH, preferably -O
H.

The poly (oxyalkylene) substituent can be any suitable divalent or trivalent group, for example, N, NR, O, S, S ₂ ,
SO ₂ N, SO ₂ NR, CO ₂ , CON or CONR
(Where R is H, C ₁ -C ₁₂ alkyl, phenyl or benzyl) by a covalent bond to the disazo colorant. Preferably, the linking group is N, NR, O, S
O ₂ N or SO ₂ NR. Two poly (oxyalkylene) substituents can be attached to the disazo colorant via a trivalent linking group.

Aromatic compounds useful in the present invention include phenyl, naphthyl and S, N
And heterocyclic compounds containing 1 to 3 heteroatoms selected from O. As further examples, based on the following structures: thiazole, benzothiazole, thiadiazole, isothiazole, isoxazole, benzisothiazole, thiene, pyridine, pyrazole, thiazole, phthalimide, pyrrole, indole, pyrimidine, thiphene and furanone Heterocyclic compounds can be used. Preferably, all aromatic groups containing disazo colorants are selected from phenyl, phenylene, naphthyl and naphthalene groups.

In addition to the poly (alkylene) substituents, the aromatic groups of the disazo colorant may have from 1 to 4 substituents, such as C _1-
C ₄ alkyl, C ₁ -C ₄ alkoxy, halogen, _{hydroxy, SO 3 H, SO 3 Na} , CO 2 R, CN, NR
_2, thiol, amide, Suruhokisamido, alkyl or arylcarbonyl, halogenated C ₁ -C ₄
It can be substituted with alkyl or aryl, provided that it is C ₁ -C ₈ alkyl or aryl. Suitable substituents can be found in the Color Index, 3rd edition,
Volume 4, C.I. I. No. 20000-99999, 413
It is also illustrated on pages 9-4276 (1971). When a disazo colorant is used to color a polyurethane resin, NO ₂ , NO, NH ₂ , NHR (where R is alkyl or aryl), SH, OH, CONH
₂ and certain substituents such as SO ₂ NH ₂ are preferably not present on the aromatic ring to avoid adverse interactions during the preparation of the resin.

Examples of disazo colorants which find utility in the present invention are as follows.

[0024]

Embedded image Here, Y is a poly (oxyalkylene) substituent and has a nucleophilic group at the terminal.

The disazo colorant is prepared using procedures well known in the art for synthesizing disazo dyes, other than using a poly (oxyalkylene) substituted coupling component or a poly (oxyalkylene) substituted diazo component. Can be synthesized. Suitable synthetic routes are described by Hines et al., US Pat. No. 5,108,460; Moody et al., US Pat.
90, 921 and the following examples.
The terms "EO" and "PO" stand for ethylene oxide and propylene oxide residues, respectively.

[0026]

【Example】

Example 1 Water (250 g), urea (6.1 g), 4,4'-diaminostilbene-2,2'-disulfonic acid (22.2
g), and m-toluidine 2EO10PO6EO (13
2.8 g) to a stirred solution of sodium nitrite (8.8 g).
g) in water (25 g) was added over 15 minutes at room temperature. The reaction mixture was stirred overnight at room temperature. Water (250 g) and methylene chloride (100 g) were added to the resulting red reaction mixture.
g) was added. The organic layer was separated. The aqueous reaction mixture was extracted with an additional 100 g of methylene chloride. The organic layers were combined and concentrated on a rotary evaporator to give a dark red oil as product. It has a maximum absorbance of 513 nm
(In MeOH).

Example 2 Water (23.0 g) 93% sulfuric acid (35.0 g), and 2-
To a stirred solution of ethylhexanol, 4,4'-diaminodiphenylsulfone (10.8 g) was added at room temperature. The resulting reaction mixture was stirred for 10 minutes and then cooled to 0-5 <0> C. Nitrosylsulfuric acid (40%, 31.0 g) was added slowly, keeping the temperature <10 ° C. After stirring for 1 hour, the mixture was tested for nitrite. Positive nitrite test results were obtained and sulfamic acid (1.8
g) was added and the pressure was reduced. After one hour, negative nitrite test results were obtained. Next, the obtained bisdiazonium salt solution was treated with m-toluidine 2EO10PO6EO (89.
8g), water (45.0 g), and urea (2.0 g) were added slowly at 0-10 <0> C. The resulting red reaction mixture was stirred overnight, after which time a 50% caustic solution (caus
tic) (60 g) was added and the pH was adjusted to 7 and above. The resulting product layer was separated, washed several times with hot water and concentrated on a rotary evaporator to give an orange oil. It had a maximum absorbance of 471 nm (in MeOH).

Example 3 The procedure of Example 2 was followed except for the amounts of reactants and individual diamines and coupling agents used. All such amounts are specified below.

Sulfuric acid 50 g Water 50 g 2-ethylhexanol 0.4 g 4,4'-diaminodiphenylsulfone 20 g Nitrosylsulfuric acid 57 g Sulfamic acid 10 g Aniline 2EO / 10PO / 6EO 163 g Water 80 g Caustic solution 85 g A yellow / orange oil was obtained, which had a maximum absorbance of 460 nm (MeOH).

Example 4 The procedure of Example 2 was followed except for the amounts of reactants and individual diamines and coupling agents used. All such amounts are specified below.

85% phosphoric acid 21 grams 93% sulfuric acid 19 grams 4,4'-methylene dianiline 17 grams 2-ethylhexanol 0.3 grams nitrosyl sulfate 61 grams sulfamic acid 5 grams m-toluidine 2EO / 10PO / 6EO 180 grams water 180 grams 50% caustic solution 125 grams A yellow-orange oil was obtained. Lambda Max (MeO
H) 426 nm.

EXAMPLE 5 Water (26.0 g), 93% sulfuric acid (52.0 g), acetic acid (91.5 g), and 2-ethylhexanol (1 g)
Was added to 4,4′-oxydianiline (21.0
g) was added at room temperature. The resulting reaction mixture was stirred for 10 minutes and then cooled to 0-10 ° C. Next, water (31.0
g) and a solution of sodium nitrite (18.0 g) were added slowly, keeping the temperature <10 ° C. After stirring for 1 hour, the mixture was tested for nitrite. Positive nitrite test results were obtained and sulfamic acid (7.5
g) was added and vacuum was applied. After one hour, negative nitrite test results were obtained. Next, the obtained bisdiazonium salt solution was added to m-toluidine 2EO10PO6EO (21
7.0 g) and water (150.0 g).
Add slowly at ° C. The resulting purple reaction mixture was stirred overnight, after which a 50% caustic solution (171 g) was added,
The pH was adjusted to 7 or higher. The product layer obtained was separated, washed several times with hot water and concentrated on a rotary evaporator to give a yellow oil. It has a maximum absorbance of 428 nm
(In MeOH).

Polymer Resins Diazo colorants can be used to color a wide range of polymer resins by the reaction of electrophiles and nucleophiles, including addition and condensation polymerizations. The nucleophilic group of the disazo colorant is
It is selected to react with at least a portion of the monomers under polymerization conditions. Examples of suitable resins include polyurethane, polyester, polyamide, epoxy, phenolic resins,
Alkyd resin, allyl resin, silicone and melamine /
Urea resin is included. Colored resins are used in a variety of ranges including soft foams, semi-rigid foams, hard foams, films, fibers, molded parts, coatings, sealants and elastomers.

Disazo colorants are used to color the polymer resin by mixing the colorant with the monomers that react to form the polymer before or during the polymerization. In many cases, it will be advantageous to premix the colorant and a portion of the monomer. For example, the colorant can be premixed with the polyol before the polyol is mixed with the polyisocyanate to produce a colored polyurethane. The disazo colorant is preferably a liquid. These can be added to the components or the reaction mixture in solvent-free form or diluted with a compatible aqueous or organic solvent.

Since the disazo colorants used in the process are themselves polymerizable components, they can be used, for example, in most polyols, most epoxy formulations, polyester formulations and themselves used in polyurethanes. Can be dissolved. This property is particularly valuable for three reasons. First, this solubility allows for rapid mixing and uniform dispersion throughout the resin, and therefore, when properly mixed, produces no shade differences and shade layers. Second, the present colorants are not prone to settling as in the case of pigment dispersion. Third, two or more colors can be blended and prepared, and a wide range of colors can be utilized.

The present invention is particularly advantageous for providing colored polyurethane resins, including thermoplastics and thermosets. The polyaddition reaction of a polyisocyanate with a polyol is well known in the art and is described in ICI Polyurethan's BooK, John Wiley a
nd Sons (1987) and Kirk-Othmer Encyclopedia of Chemical Technology (Encyclopedia o)
f Chemical Technology) Third Edition, Vol. 23, 576-
608 (1983). In addition to polyurethane, polyol and disazo colorants, catalysts such as tertiary amines and organometallic compounds, and small amounts of surfactants may also be present.

[0037] The colored polyurethane resin can be obtained by adding a colorant to the polyol or diol component of the reaction mixture or to one of the other components, but is preferably added to the polyol component. Polyols are polyesters containing hydroxyl groups, especially those which are the reaction product of an alcohol containing two hydroxyl groups and a dibasic carboxylic acid, or polyethers containing hydroxyl groups, especially ethylene oxide, propylene oxide, styrene oxide or epiester. Chlorohydrin,
It can be the product when added to water, alcohol or amine, preferably dialcohol. Coloring agents can also be admixed with so-called chain-extending diols, such as ethylene glycol, diethylene glycol and butylene glycol. Generally, it is desirable not to use more than 20% by weight of the disazo colorant based on the weight of the polyol.

In the next step of the reaction, the polyol and the polyisocyanate are mixed with one another. The reactants are (according to the method disclosed for producing polyurethane products)
They are mixed together as in reaction injection molding (RIM).

The disazo colorant is used in the colored resin
0.005 to 10 wt%, preferably 0.1 to 4 w
It is added to the polymerizable mixture of monomers or their individual components to achieve a final concentration of t%.

The disazo colorants disclosed herein have the advantage that, due to their enhanced reactivity, the level of extraction can be reduced when incorporated into the polyurethane resin. At the same time, disazo colorants have a lower viscosity compared to similar compounds prepared with chloropropanediol or glycidol-based coupling agents.

Example 6A The following procedure was used. First, the color values for the tested colorants range from 0.15 to 0.20 grams of colorant by 100.
Determined by placing in a ml volumetric flask and adding about 40-50 ml of methanol. The flask was swirled until the colorant was dissolved, after which more methanol was added until the 100 ml mark on the flask.
The flask was stoppered, the contents mixed and shaken. next,
Exactly 2.0 ml of this colorant in methanol is added to another 1
Into a 00 ml flask, methanol was added up to the 100 ml mark of the flask, stoppered and shaken.

The Beckman DU-650 spectrometer was zeroed with methanol, filled with the test solution, and the solution was scanned from 300 to 700 nm. The maximum absorbance was recorded. The color value is obtained by multiplying the sample weight by 0.2 and dividing the obtained value by the value of the maximum absorbance.

To correct the color intensity, the compared colorants were all cut to a color value consistent with the polyester polyol diluent (Fomrez 11-225® available from Witco). This is achieved by taking a known amount of colorant having a known color value. The amount of diluent added is determined as follows.

[(Excluded CV / desired excluded CV) -1] (weight of non-excluded colorant) = weight of Formez® added Reactivity of the disazo colorant is 0.95 TDI index Per 100 parts of a polyester formulation having
p) Tested in 4 parts.

4 g of the orange colorant, adjusted to a color value of 21 and shown in Table 1 below, was added to 100 g of polyester polyol (Witco 53®, mw-3500)
Added. This was treated with n-ethylmorpholine (32.5
%), Water (50.9%), silicone L-532® (14.2%), and Baircat B-16®
(2.4%) of a solution consisting of 7.0 ml. next,
34.2 g of toluene diisocyanate (80/2
0) was allowed to react under ambient conditions for about 2 minutes. Next, the foam was cured at 130 ° C. for 15 minutes and at room temperature for 48 hours.

After the foams were cured, they were tested for extractability using the following method. One gram of foam was removed from the center of the polyurethane bun. This material is then immersed in 75 ml of ethanol in a glass jar,
Plugged and extracted for 4 hours. The glass jar was shaken every 30 minutes so that the foam remained soaked. The amount of colorant extracted from the foam was measured using Beckman DU-650.
It was determined by measuring the absorbance of the extraction solution with a spectrometer. The results of the extraction are shown in Table 1 below.

[0047]

[Table 1]

Example 6B (Comparative) The disazo colorant of the present invention was prepared according to US Pat. No. 4,284,729.
(Example # 6B-1) or US Pat. No. 5,290,521
The procedure of Example 6A was repeated, except that the orange color former corresponding to (Example # 6B-2) was replaced. The structure and results of the colorant are shown in Table 2 below.

[0049]

[Table 2]

Example 7A The procedure of Example 6A was repeated except that the yellow disazo colorant shown in Table 3 below was used.

[0051]

[Table 3]

Example 7B (Comparative) Example 6B was repeated except that the yellow monoazo colorant shown in Table 4 below was used.

[0053]

[Table 4]

Example 8A Example 6A was repeated except that the red disazo colorant shown in Table 5 below was used.

[0055]

[Table 5]

Example 8B (Comparative Example) Example 6B was repeated except that the red monoazo colorant shown in Table 6 below was used.

[0057]

[Table 6]

The results of Examples 6 to 8 show that the disazo colorants of the invention are more reactive and therefore have significantly lower extraction levels than the comparative monoazo example. On average, conventional poly (oxyalkylene) -substituted colorants with unbranched chains are more than 20 times more extractable than disazo colorants with poly (oxyalkylene) substituents at each end of the disazo chromophore. And a colorant having a branched chain is five times or more extractable.

Of course, there are many other modifications and aspects of the present invention, which are intended to be included within the scope of the following claims.

[0060]

The colorant of the present invention is liquid under ambient environmental conditions, is easy to handle, enables rapid mixing, and enables the colorant of the present invention to be uniformly dispersed throughout the resin. Thus, if properly mixed, there will be no shading and shading layers. The present colorant does not have a tendency to precipitate as in the case of dispersing a pigment. It can be prepared by blending two or more colors, a wide range of colors is available, and is not as easily extracted from the polymer as compared to prior art colorants. Disazo colorants have higher poly (oxyalkylene) substituents than prior art colorants, despite the fact that the poly (oxyalkylene) substituents contained therein are not branched and have poly (oxyalkylene) substituents at each end. Not substantially viscous. Further, the colorants of the present invention can be incorporated and grafted into the backbone of the polymer resin.

 ─────────────────────────────────────────────────── ─── Continued on front page (72) Inventor Mark E. Lugsdale, Dobson Road, Duncan, 29334, United States, United States 260 (72) Inventor David Jay Moody, United States, 29302, South Carolina, Spartan Burg, Garden Glove Court 409

Claims (10)

[Claims] 1. A process for producing a colored polyurethane, comprising: (a) a disazo coloration having a poly (oxyalkylene) substituent attached to each end of a polyol, a polyisocyanate, a catalyst and a disazo chromophore. Providing a reaction mixture of agents wherein each poly (oxyalkylene) substituent has from 2 to 200 alkylene oxide residues and a nucleophilic end group capable of reacting with the polyisocyanate; and (b) A method comprising polymerizing a polyol, a polyisocyanate and a disazo colorant to form a polyurethane, whereby the disazo colorant is covalently bonded into the polyurethane. 2. The method of claim 1 wherein each poly (oxyalkylene) substituent contains from 4 to 75 alkylene oxide residues, the terminal group is a hydroxyl group, and each poly (oxyalkylene) Alkylene) substituents are random or block copolymers of ethylene oxide and propylene oxide. 3. The method according to claim 2, wherein the disazo colorant is selected from the group consisting of compounds having the following structure: Where Y is a poly (oxyalkylene) substituent. 4. The method according to claim 1, wherein the disazo colorant is selected from the group consisting of compounds having the following structure: Embedded image Where Y is a poly (oxyalkylene) substituent. 5. The method of claim 4, wherein each poly (oxyalkylene) substituent is a block copolymer of ethylene oxide and propylene oxide, having a total of from 4 to 35 alkylene oxide residues. 6. A colored polyurethane containing a disazo colorant having a poly (oxyalkylene) substituent covalently bonded to each terminal disazo chromophore, wherein each poly (oxyalkylene) substituent is From 2 to 20
Those having 0 alkylene oxide residues and a nucleophilic end group covalently bonded in the polyurethane. 7. The colored polyurethane of claim 6, wherein each poly (oxyalkylene) substituent contains from 4 to 75 alkylene oxide residues selected from ethylene oxide and propylene oxide. 8. The colored polyurethane according to claim 7, wherein the disazo colorant is selected from the group consisting of compounds having the following structure. Embedded image Where Y is a poly (oxyalkylene) substituent. 9. The colored polyurethane of claim 6, wherein the disazo colorant is selected from the group consisting of compounds having the following structure: Embedded image Where Y is a poly (oxyalkylene) substituent. 10. The colored polyurethane of claim 9, wherein each poly (oxyalkylene) substituent is:
A block copolymer of ethylene oxide and propylene oxide having a total of 4 to 35 alkylene oxide residues.